This magic boot comes packed with (sole)ful historical significance. But that doesn’t mean that it falls into the antique category. In fact, it’s far from it. Our best boot brands are reinventing the seasonless trend with contemporary attitudes contrasted with classical silhouettes.

Born from a direct request from Queen Victoria, Chelsea boots have made their way into celebrity circles ever since. And while the Queen saw them as a functional necessity for long days out on horseback, the Beatles and Rolling Stones made them a famous fashion statement. We can’t help but agree with both parties. Named after the London town, Chelsea boots are still loved worldwide for their comfortable-but-chic character.

These ankle-length boots are distinguished by their elasticated side panels for easy dressing (say goodbye to tedious lace-ups). While pull-up tags take out any effort altogether. And indented rubber lug soles are not only stylish to boot—they’re made for a lifetime of wear. But besides these iconic features, these slip-on boots for women come in all shapes and sizes. And our best boot brands never fail to excite us with cutting-edge designs.  All in all, it’s difficult not to fall in love with each of these brands for their unique take on the Chelsea boot. And we’re almost certain that your perfect pair is just to be stepped into.

But that’s enough talking. Let’s get walking.

Koio
Koio

Koio: Best overall women’s Chelsea boots

They’re versatile. They’re comfortable. And they’re stylish to boot. Koio ticks every box when it comes to Chelsea boots. Handcrafted in Italy, the water-resistant lug sole is light on your feet. And it adds a contemporary edge to the timeless shoe. While the elasticated side panels allow for ample stretch. The sleek Nero tone complements every ensemble.

These Koio Chelseas are more than just a closet staple. They’re the perfect pair for every occasion.

Best for: Season-to-season style.

SHOP AT KOIO | $365

Material: Leather
Color: Black
loft
loft

Loft: Best Chestnut Brown Chelsea Boot

Lug soles step these wear-with-everything, chic and easy Chelsea boots up with cool-girl attitude. Padded footbed for comfort. 1 1/3″ heel.

SHOP ON: THE LOFT | $138

Material: Suede
Color: Chestnut Brown and Black
Net a porter
Net a porter

Isabel Marant Castay: Best designer Chelsea boots for women

These timeless Castay’s effortlessly defeat seasonal trends with their classical style. And we don’t think that you could outwear the lugged rubber sole even if you tried. The black leather has a subtle shine to contrast the chunkier shoe. And there’s nothing that the simple-yet-chic silhouette can’t achieve when it comes to complementary shoes.

These Chelsea boots will ground your designer denims with the same subtle sophistication as they do your dresses. And they’ll amp up your Autumn wardrobe in typical Isabel Marant fashion.

Best for: Doing the groundwork for fashionable getups.

SHOP ON NET-A-PORTER | $750

 

Material: Leather
Color: Black
dr martens
dr martens

Dr Martens: Best value women’s Chelsea boots

Famous for their chunky black boots—Dr Martens does it again with this stretchy laceless rendition of the old-school classic. Born in 1461, the timeless brand definitely isn’t new to the shoe game. And their durable designs beg to be passed down to future generations. While the iconic label flaunts the well-known logo, we’re pretty sure you can spot the brand’s classical silhouette from a mile away.

These Chelsea boots carry the same big attitude as their lace-up counterparts. But they provide a new functionality with an effortless slip-on style.

Best for: Chunky classics with a twist.

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Material: Leather
Color: Black

 

M gemi
M gemi

M.Gemi The Noemi: Best leather ankle boots for women

Proof that you can have the best of both worlds, The Noemi marries outdoor functionality with everyday elegance. The pull tab vouches for seamless slip-ons. While the Italian quality craftsmanship synonymous with M.Gemi will tackle any day on foot.

This slightly lower ankle boot is flawlessly flattering on every leg shape. And these Chelseas by M.Gemi will add that extra spring to your step (yes, even in the colder months).

 

Best for: (Sole)ful sophistication.

SHOP AT M.GEMI | $195

Material: Leather
Color: Black

 

far fetch
far fetch

Legres Garden: Best women’s Chelsea boots for walking

These boots were made for walking. Rumor has it the ‘96 hit single is referring to this pair of booties.

OK, we made that up. But you would think so too, after a day on the town in these Chelseas.Honoring the rich history of Italian craftsmanship, practicality has never looked so perfect. The soft, leather fabric is accompanied by elasticated sides for extra stretch. And the sturdy soles will never grow old.

Best for: Making walking the walk a breeze.

SHOP ON FARFETCH | $535

 

Material: Suede
Color: Black

 

zappos 1
zappos 1

Blundstone BL510 Original 500: Best Chelsea work boots for women

Double pull-up tags mean double the fun. They’re the perfect protective boots for outdoor wear. But they’ll also take you to post-work drinks with an edgy attitude. The durable soles are made to tackle every track or trail. And waterproof leather deems volatile weather unproblematic. Shock absorbant midsoles provide a softer landing. And the dark neutral colorway speaks to a modern, versatile functionality.

So whether you’re taking them camping for the weekend or celebrating the weekend with a glass of wine—these beautiful boots are your new best friends.

Best for: BBF (Best Boots Forever).

SHOP ON ZAPPOS | $200

Material: Leather
Color: Black

 

Frye
Frye

Frye Sabrina: Best brown Chelsea booties for women

A soft, handworked tan leather adds a country flair to a classical silhouette. And if you’re looking for a stylish lift to get you through Winter, these block heeled beauties (booties) know just how to do it. Pair them with light flowy florals or tighter denims. The neutral colorway only ever adds an air of subtle sophistication.

And these elevated brown boots will fit right into your Autumn wardrobe (cue the pumpkin spice latte!)

Best for: Beating Winter blues with boots.

SHOP ON ZAPPOS | $400

Material: Leather
Color: Brown

 

proenza
proenza

Proenza Schouler: Best women’s chunky boots

Proenza Schouler knows how to take the latest trends to new heights. And this chunky pair is no exception. The ankle-length silhouette is accented with an asymmetrical toe. And a (very) thick tread sole is bound to make a statement (prepare for the compliments).

Get a pair of these black bold booties to flaunt your forward-thinking eye for fashion. Or opt for the white design to really make your mark in stylish circles.

Best for: Standout fashion statements.

SHOP ON FARFETCH | $995

Material: Leather
Color: Black and white

 

gucci
gucci

Gucci: Best luxury Chelsea boots for women

There’s no need to accessorize when wearing a pair of these glamorous Guccis. The detachable ankle belt embellished with sparkling crystals will do it all for you. The unique gems resemble vintage jewels. And they speak to the timeless modernism inherent to the luxurious brand.

These opulent details are flawlessly contrasted with a Chelsea lug sole for refined-but-fierce finesse. While the signature Double G is all you need to finish off the shiny black look.

Best for: Gucci glamor takes on vintage gems.

SHOP AT GUCCI | $1,230

Material: Leather
Color: Black
WHBM
WHBM

WHBM Military Bootie: Best heeled women’s Chelsea boots

Comfortable heels—not an oxymoron when trying on a pair of WHBM’s Military Booties. And we’re pretty sure you’ll agree when you will be strutting around cobbled pavements without a care in the world.

This simple silhouette finds its voice in sharp details like the commanding presence of Military-inspired metal buttons and a stiletto heel. Pair these comfortable Chelsea boots by WHBM with red-painted lips, and you’re bound to feel like a million bucks.

Best for: A refined rendezvous.

SHOP ON WHBM | $200

Material: Suede
Color: Black
tod
tod

Tod’s: Best suede leather ankle boots for women

Our best ankle boots come in all shapes and sizes. This one comes in the form of a velvety suede Chelsea boot. The opulent fabrication of the typical design speaks to the brand’s luxurious reputation. And the versatile style means that you can wear the same pair every day of the week (hello capsule wardrobe!).

Pair these Tod’s Chelseas with black neutrals or vibrant hues in any form. These accommodating boots make layered dressing easy by complementing every piece in the ensemble.

Best for: Effortless pairing.

SHOP ON MYTHERESA | $795

Material: Suede
Color: Black
st laurent
st laurent

Saint Laurent Theo: Best suede heeled Chelsea boot for women

Wake up feeling low? Put on your (black) suede shoes and make the day your catwalk. These thick heels are bound to take your outfits to new heights and boost your confidence. The suede fabric speaks to a refined sophistication. And pointed toes will keep everyone around you in check.

These sumptuous Chelseas are the perfect companions for public speeches, first dates or just about anything where you could do with an extra lift.

Best for: Carefree confidence.

SHOP ON FARFETCH | $995

 

Material: Suede
Color: Black

 

white 1
white 1

Elleme Chouchou: Best white Chelsea boots for women

We all know that the devil is in the details. But Chouchou detailing is the holy grail of luxurious design. And this white leather pair couldn’t do it better. The clean colorway is complemented by a subtle ruched accented heel. Elongated elasticated sides take the classic Chelsea stretch even further. And a thick rubber lining exudes a playful but (sole)ful attitude.

These decadent details are enough to make every fashionista fawn over this designer pair of Chelseas We know that we are.

Best for: Pure white hues marry devilishly tempting details.

SHOP ON 24S | $499

Material: Leather
Color: White
Gianvito Rossi
Gianvito Rossi

Gianvito Rossi: Best cream women’s Chelsea boots

They’re your new mom-jean accomplice for a casual chic day-out style. The soft cream hue perfectly contrasts the rugged edges and chunky soles. The culmination is a masterpiece of cheeky-feminine minimalism. Made in Italy, the beige calf leather silhouette extends beyond the ankle. It’ll slimly tuck beneath your looser denim. And the elongated elasticated panels make for easy dressing.

Following in his father’s Versace footsteps, this pair of Chelseas is proof that Gianvito Rossi has stepped out (pun intended) on his own successfully.

Best for: Soft hues get a cheeky chunky makeover.

SHOP ON NET-A-PORTER | $1,095

Material: Leather
Color: Cream
Nisolo
Nisolo

Nisolo Everyday: Best women’s tan Chelsea boots

Short but sweet—this tan pair would melt your leather-loving heart. The lighter honey tone flawlessly accompanies every ensemble. They add a sophisticated flair without stealing the show. And the lower ankle is a flattering fit for every leg type. But the soft, buttery boots are more than just a fashion statement. All of their leather is sustainably sourced. And ethical shoemaking is at the forefront of the sustainable brand.

This versatile pair of Chelseas is endlessly functional with waterproof leather and neutral hues.

Best for: Form and function merge to create an everyday masterpiece.

SHOP AT ZAPPOS| $200

Material: Leather
Color: Tan
Valentino
Valentino

Valentino Garavani: Best platform Chelsea boots for women

Extra height? Check. All-day comfort? Yes! What more could you want in a pair of Chelseas? Described as jet-set chic, this Italian brand knows how to make a statement with bold features. And these huge soles are prime examples. While the rest of the shoe remains relatively simple.

This black leather silhouette is on the top of our list of most comfortable boots for women. And at the same time, they are guaranteed to attract a strew of compliments.

Best for: A simple silhouette showcases unsubtle soles.

SHOP ON 24S | $995

Material: Leather
Color: Black

 

Blundstone #1477
Blundstone #1477

Blundstone #1477: Best waterproof women’s Chelsea boots

They’re the once-off purchase that will make the rest of your life a lot easier. These Blundstone Antiques make outdoor living effortlessly simple. They’re made for long day-outs. And are ready to tackle anything thrown at them—including heavy downpours. The dark brown leather adds a masculine touch to an otherwise feminine silhouette.

These weathered Chelseas may flaunt a vintage flair. But they’re designed with all the latest technology to make every step luxurious. We think of them as a pair of perfect opposites.

Best for: Weathering the elements.

SHOP ON ZAPPOS | $240

Material: Leather
Color: Brown
Ganni
Ganni

Ganni: Best women’s chelsea rain boots

These gorgeous chunky soles are the ultimate rain boots. Made from durable, waterproof rubber, they’re designed to endure any weather. The multifunctional boot flaunts all the facets of your typical Chelsea. But the contemporary brand has added its own modern flair. The silhouette is slightly higher and comes in sleek black or soft green hues.

These versatile Gannisare designed for rain. But we give you full permission to wear them in the bright sunshine too.

Best for: Enduring in an effortless style.

SHOP ON FARFETCH | $196

 

Material: Rubber
Colors: Black and green